Combined Dynamic Kinetic Resolution and C-H Functionalization for Facile Synthesis of Non-Biaryl-Atropisomer-Type Axially Chiral Organosilanes
| Autor: | Xu Wang, Li-Wen Xu, Jun-Han Ma, Lu-Lu Han, Zheng Xu, Yu-Ming Cui, Zhao Li, Li-Lei Fang, Qin Yang |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Atropisomer
010405 organic chemistry Organic Chemistry chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Stereocenter Kinetic resolution chemistry.chemical_compound chemistry Molecule Surface modification Palladium Organosilicon |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 27(13) |
| ISSN: | 1521-3765 |
| Popis: | Although asymmetric C-H functionalization has been available for the synthesis of structurally diverse molecules, catalytic dynamic kinetic resolution (DKR) approaches to change racemic stereogenic axes remain synthetic challenges in this field. Here, a concise palladium-catalyzed DKR was combined with C-H functionalization involving olefination and alkynylation for the highly efficient synthesis of non-biaryl-atropisomer-type (NBA) axially chiral oragnosilanes. The chemistry proceeded through two different and distinct DKR: first, an atroposelective C-H olefination or alkynylation produced axially chiral vinylsilanes or alkynylsilanes as a new family of non-biaryl atropisomers (NBA), and second, the extension of this DKR strategy to twofold o,o'-C-H functionalization led to the multifunctional axially chiral organosilicon compounds with up to >99 % ee. |
| Databáze: | OpenAIRE |
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